voriconazole

Trade name: vfend

Small moleculeapproved

Approved

May 24, 2002

Voriconazole (vor-i-KON-a-zole, brand name Vfend, Pfizer) is a triazole antifungal medication. VFEND® (voriconazole) is available as film-coated tablets for oral administration, and as a lyophilized powder for solution for intravenous infusion. Voriconazole is a triazole antifungal agent indicated for use in the treatment of fungal infections including invasive aspergillosis, esophageal candidiasis, and serious fungal infections caused by Scedosporium apiospermum (asexual form of Pseudallescheria boydii) and Fusarium spp. including Fusarium solani. Fungal plasma membranes are similar to mammalian plasma membranes, differing in having the nonpolar sterol ergosterol, rather than cholesterol, as the principal sterol. Membrane sterols such as ergosterol provide structure, modulation of membrane fluidity, and possibly control of some physiologic events. Voriconazole effects the formation of the fungal plasma membrane by indirectly inhibiting the biosynthesis of ergosterol. This results in plasma membrane permeability changes and inhibition of growth. The primary mode of action of voriconazole is the inhibition of fungal cytochrome P-450-mediated 14 alpha-lanosterol demethylation, an essential step in fungal ergosterol biosynthesis. The accumulation of 14 alpha-methyl sterols correlates with the subsequent loss of ergosterol in the fungal cell wall and may be responsible for the antifungal activity of voriconazole. Voriconazole has been shown to be more selective for fungal cytochrome P-450 enzymes than for various mammalian cytochrome P-450 enzyme systems. The most common side effects associated with voriconazole include transient visual disturbances, fever, rash, vomiting, nausea, diarrhea, headache, sepsis, peripheral edema, abdominal pain, and respiratory disorder. Unlike most adverse effects, which are similar to other azole antifungal agents, visual disturbances (such as blurred vision or increased sensitivity to light) are unique to voriconazole. Though rare, there have been cases of serious hepatic reactions during treatment with voriconazole (a class effect of azole antifungal agents). Liver function tests should be evaluated at the start of and during the course of therapy. Voriconazole is phototoxic. It has been associated with an increased risk of squamous-cell carcinoma of the skin — NCATS

Clinical trial activity

123 trials · 129 clinical orgs · 34 marketing orgs

Phase 1
36
Phase 2
52
Phase 3
35
Phase 4
24

Earliest trial started Jun 1, 1997 (NCT00003031)

Timeline

1990s

  1. Aug 1, 1995

    Pfizer — IND Organization

  2. Aug 1, 1995

    Pfizer — IND Organization

  3. Jan 1, 1997

    Earliest Phase 3 Sponsor(trial)

2000s

  1. Jan 1, 2000

    Earliest Phase 1 Sponsor(trial)

  2. May 24, 2002

    Pfizer — Earliest FDA Approval

  3. May 24, 2002

    Pfizer — NDA Organization

  4. Jan 1, 2003

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Apr 22, 2010

    Mylan — Marketing Organization

  2. Dec 12, 2011

    Sandoz — Marketing Organization

  3. Dec 12, 2011

    Novartis — Marketing Organization

  4. Apr 6, 2012

    Teva — Marketing Organization

  5. Sep 2, 2015

    Glenmark Pharmaceuticals — Marketing Organization

  6. Jan 22, 2016

    Aurobindo Pharma — Marketing Organization

  7. Mar 23, 2016

    Alvogen — Marketing Organization

  8. Mar 23, 2016

    Almaject — Marketing Organization

  9. Apr 13, 2016

    Amneal Pharmaceuticals — Marketing Organization

  10. May 24, 2016

    Ajanta Pharma Ltd — Marketing Organization

  11. May 24, 2016

    Appco Pharma — Marketing Organization

  12. May 24, 2016

    Novel Anti-Infective Technologies, LLC — Marketing Organization

  13. May 24, 2016

    Zydus Discovery DMCC — Marketing Organization

  14. May 24, 2016

    Cadila Healthcare — Marketing Organization

  15. May 24, 2016

    Rising Pharmaceuticals — Marketing Organization

  16. May 24, 2016

    Chartwell Pharmaceuticals — Marketing Organization

  17. Aug 8, 2016

    Prinston Inc — Marketing Organization

  18. Sep 7, 2016

    Akorn, Inc. — Marketing Organization

  19. Sep 7, 2016

    Epic Pharma Llc — Marketing Organization

  20. Mar 9, 2017

    Xellia Pharmaceuticals — NDA Secondary Org

  21. Mar 9, 2017

    Novo Nordisk — NDA Secondary Org

  22. Mar 9, 2017

    Hikma — Marketing Organization

  23. Nov 30, 2018

    Hainan Poly Pharm — Marketing Organization

  24. Nov 30, 2018

    SLATE RUN PHARMA — Marketing Organization

2020s

  1. Mar 31, 2020

    Gland Pharma Ltd — Marketing Organization

  2. Mar 31, 2020

    Fosun — Marketing Organization

  3. May 9, 2022

    Meitheal — Marketing Organization

  4. Oct 11, 2022

    PHARMOBEDIENT — Marketing Organization

  5. Feb 2, 2023

    Eugia Pharma — Marketing Organization

  6. Mar 9, 2023

    UBI Pharma Inc. — Marketing Organization

  7. Jan 2, 2024

    ZHEJIANG POLY PHARM — Marketing Organization

  8. Apr 3, 2024

    Aspiro — Marketing Organization

  9. Aug 8, 2025

    Hetero Labs Ltd — Marketing Organization

Indications

Studied for

Mechanism of action

Approval history

  • approvedMay 24, 2002

Chemistry & pharmacology

Loading structure…

SMILES

C[C@@H](C1=NC=NC=C1F)[C@](O)(CN2C=NC=N2)C3=CC=C(F)C=C3F
Mol. weight
349.3105 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Sources

Also known as

  • (r-(r*,s*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
  • (r-(r*,s*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
  • uk109496
  • uk 109496
  • uk-109496
  • uk-109496
  • uk-109496
  • vcz
  • vcz
  • vfend
  • vfend
  • vfend
  • vfend
  • voriconazol
  • voriconazol
  • voriconazol
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazole
  • voriconazolum
  • voriconazolum

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06680544Phase 2Nov 15, 2024Sheikh Zayed Medical College
NCT06582186Phase 4Oct 31, 2024University of Grenoble
NCT06493409Phase 1Aug 26, 2024Bristol-Myers Squibb
NCT05458102Phase 1Aug 19, 2022Gilead Sciences
NCT05264142Phase 1Apr 1, 2022University of Geneva
NCT05708625Phase 3Jan 1, 2022Zagazig University
NCT05268718Early Phase 1 (Phase 1)Aug 1, 2021Zhejiang University
NCT04865419Phase 1/Phase 2 (Phase 2)Jun 11, 2021AstraZeneca, University of Texas at Houston
NCT04876716Phase 3May 11, 2021Erasmus University Rotterdam, HOVON - Dutch Haemato-Oncology Association, ZonMw: The Netherlands Organisation for Health Research and Development
NCT04752163Phase 1/Phase 2 (Phase 2)Mar 25, 2021University of Texas at Houston
NCT04824417Phase 3Mar 1, 2021Postgraduate Institute of Medical Education and Research
NCT04551963Phase 1Nov 15, 2020BeOne Medicines
NCT04576325Phase 1Nov 2, 2020TFF Pharmaceuticals, TFF Pharmaceuticals, Inc.
NCT04552353Phase 4Jun 13, 2020Yung Shin Pharm. Ind. Co., Ltd.
NCT05330000Phase 1May 22, 2020Qingdao University
NCT04229303Phase 1Feb 29, 2020Zambon
NCT04238884Phase 4Jan 2, 2020Universidad Autonoma de Madrid
NCT04072640Early Phase 1 (Phase 1)Jan 1, 2020Wenzhou Medical University, Zhejiang University
NCT04872231Phase 1Nov 22, 2019TFF Pharmaceuticals, TFF Pharmaceuticals, Inc.
NCT04145583Phase 1Nov 15, 2019Haisco Pharmaceutical, Soochow University
Showing 20 of 123 trials
Page 1 / 7

Organizations

Research & Development (129)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
PfizerFor profit292441998
National Cancer Institute (NCI)Government10741999
Aravind Eye HospitalAcademic/Hospital5132007
Seoul National UniversityAcademic/Hospital5522008
University of Texas at HoustonAcademic/Hospital5332001
University of California, San FranciscoAcademic/Hospital4422007
AstellasFor profit3322006
Dartmouth UniversityAcademic/Hospital3022007
National Heart, Lung, and Blood Institute (NHLBI)Government3132001
National Institute of Allergy and Infectious Diseases (NIAID)Government3311997
National Institutes of Health (NIH)Government3122008
TFF Pharmaceuticals, Inc.For profit3322019
Zhejiang UniversityAcademic/Hospital3222014
All India Institute of Medical SciencesAcademic/Hospital2212008
Basilea PharmaceuticaFor profit2012006
Blood and Marrow Transplant Clinical Trials NetworkAcademic/Hospital2022001
Bristol-Myers SquibbFor profit2212009
Duke UniversityAcademic/Hospital2122001
Erasmus University RotterdamAcademic/Hospital2112009
Johns Hopkins UniversityAcademic/Hospital2122001
129 organizations
Page 1 / 7

Marketing (41)

OrganizationOrg typeRelationshipDate
Ajanta Pharma LtdFor profitMKTGMay 24, 2016
Akorn, Inc.For profitMKTGSep 7, 2016
AlmajectFor profitMKTGMar 23, 2016
AlvogenFor profitMKTGMar 23, 2016
AlvogenFor profitSYNMar 23, 2016
Amneal PharmaceuticalsFor profitMKTGApr 13, 2016
Appco PharmaFor profitMKTGMay 24, 2016
Appco PharmaFor profitSYNMay 24, 2016
AspiroFor profitMKTGApr 3, 2024
Aurobindo PharmaFor profitMKTGJan 22, 2016
Cadila HealthcareFor profitMKTGMay 24, 2016
Chartwell PharmaceuticalsFor profitMKTGMay 24, 2016
Epic Pharma LlcFor profitMKTGSep 7, 2016
Eugia PharmaFor profitMKTGFeb 2, 2023
FosunFor profitMKTGMar 31, 2020
Gland Pharma LtdFor profitMKTGMar 31, 2020
Gland Pharma LtdFor profitSYNMar 31, 2020
Glenmark PharmaceuticalsFor profitMKTGSep 2, 2015
Hainan Poly PharmFor profitMKTGNov 30, 2018
Hainan Poly PharmFor profitSYNJan 2, 2024
Hetero Labs LtdFor profitMKTGAug 8, 2025
HikmaFor profitMKTGMar 9, 2017
MeithealFor profitMKTGMay 9, 2022
MylanFor profitMKTGApr 22, 2010
MylanFor profitSYNOct 11, 2022
NovartisFor profitMKTGDec 12, 2011
Novel Anti-Infective Technologies, LLCFor profitMKTGMay 24, 2016
Novo NordiskFor profitNDA2Mar 9, 2017
PHARMOBEDIENTFor profitMKTGOct 11, 2022
PfizerFor profitSYNMay 24, 2002
PfizerFor profitNDAMay 24, 2002
PfizerFor profitINDAug 1, 1995
Prinston IncFor profitMKTGAug 8, 2016
Rising PharmaceuticalsFor profitMKTGMay 24, 2016
SLATE RUN PHARMAFor profitMKTGNov 30, 2018
SandozFor profitMKTGDec 12, 2011
TevaFor profitMKTGApr 6, 2012
UBI Pharma Inc.For profitMKTGMar 9, 2023
Xellia PharmaceuticalsFor profitNDA2Mar 9, 2017
ZHEJIANG POLY PHARMFor profitMKTGJan 2, 2024
Zydus Discovery DMCCFor profitMKTGMay 24, 2016